2c-b-fly / 2c-b-dfly

[illuminati boy]

After having UTFSE and found only a few passing references to this compound, one decided to post it here along with some available information about this semi-novel agent. It is hoped that additional scholarly and/or empirical data can be collected here, as it appears that in the fairly near future this one will be quite ‘out and about.’

(Monte, et al., 1996), (Shulgin, 2003), & (Shulgin, 2004) appear to be good starting points for lit searches. Below is a paper from Dr. Shulgin’s 2004 Tucson presentation.

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From the working draft of an upcoming book by Shulgin, "Psychedelic Index", Transform Press, 2004


Names:

2C-B-FLY
1-(8-Bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane


Registry Numbers:

CARN
HCL salt 178557-21-6


Natural sources:

Not known in nature


Synthesis:

From hydroquinone (with 1-chloro-2-bromoethane) to 1,4-bis(2-chloroethoxy)benzene (with Br2) to 1,2-bis(2-chloroethoxy)-2,5-dibromobenzene (with BuLi) to 2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran (with dichloromethyl methyl ether) to 4-formyl-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran (with CH3NO2) to 4-(2-nitro-1-ethylene)-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran (with LAH) to 1-(2,3,6,7-Tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane (with Br2) to 2C-B-FLY (Monte, et al., 1996).


History:

The "FLY" name was inspired by the two dihydrofuran rings that extend oppositely from the sides of the benzene ring. When they are aromatized (furan rings) they are planar with the benzene ring and the code name is "DRAGONFLY" and they are listed as DFLY derivatives.


Physical properties:

C12 H14 Br N O2
HCl salt m.p. >310 (EtOH, EtOAc) (Monte, et al. 1996).


Pharmacology:

The five "FLY" compounds (2C-FLY, 2C-B-FLY, FLY, B-FLY and DOM-FLY) were assayed in a drug discrimination paradigm with LSD-trained rats, and in interactions with various serotonin receptors. (Monte, et al., 1996).
2C-B-FLY is active in man at an oral dose of 10 milligrams (Shulgin, 2003a)


Legal Status:

2C-B-FLY is not listed in any law.

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http://www.nis.atr.jp/~ray/pubs/Tucson04/2C-B-fly.html
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Also one has heard that either 2C-B-FLY or 2C-B-DFLY was reportedly Ann’s favorite phenethylamine. This was 2nd hand and has not yet been confirmed. It is hoped that additional empirical, anecdotal, and/or other information can be contributed to this thread.

[fastandbulbous]

Well from what I've read, and extending info from other fly & dragonfly compounds, I'd imagine that 2C-B FLY will be pretty much identical to 2C-B, only active at a lower dose. 2C-B DRAGONFLY might be another damp squib as it seems that the fully aromatic compounds lose a lot of their activity when taken orally.

Despite the higher receptor affinities of the DFLY compounds, I think it's the fly compounds that'll be the ones to make the impact on more widespread research

[nndmt]

...

[nuke]

Really? There was someone here who said they injected some (r)-br-dfly and it was active at about 200ug IV...so for the corresponding 2 carbon homologue to have the same dose would be unexpected..

190ug IV (racemic br-dragonfly) - color shifting, sparkles, very mild visually. No mental or tactile effects, no euphoria. Didn't seem to last more than 30 minutes

http://www.bluelight.ru/vb/showthrea...y&pagenumber=2

[illuminati boy]

Well one has heard from at least 2 different sources that Ann was quite impressed with at least one of the 2C-B-FLYs. A comment to that effect was posted here at BL and one forgets exactly where the other source was. But simply note the timeframe for the writing of PIHKAL and roughly when 2C-B-FLY came into existence. It is certainly possible that one could change their mind at a later date once presented with new data to consider… Still whatever the situation, a single person’s experience, good or bad, could easily be idiosyncratic.

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Referenced thread:
http://www.bluelight.ru/vb/showthrea...35#post3326535

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[Coolio]

nuke, I made that report and I don't consider it to be active at that dose. It could have easily been placebo effect (I get color shifting and sparkles if I stare at a white surface and think about psychedelic visuals while I'm sober), and I did not feel any of the telltale physical signs of having ingested a serotonergic drug.

[illuminati boy]

Beyond Shulgin’s Tucson paper, the only other bit of information (about humans anyway) I was able to get a hold of was a couple 2nd hand reports that Sasha said it was Ann’s favorite phenethylamine. I consider 2nd hand anything about as reliable as chiromancy, but it still piqued my interest.

Theoretically one might expect that it may be similar to 2C-B, but with some degree of increased potency. That says something but not all that much. PiHKAL gives 2C-B dosing as 12 - 24 mg. and Shulgin’s Tucson paper lists list activity at 10 mg. for 2C-B-FLY, so maybe a 10-30% increase in potency? Pure guesswork here.

Practically, since the number of non-rats to ingest this is likely far less than 100, one may want to consider starting at 1 mg. or less for a first try. The simple fact is that this one is a very big questionmark at this time. It is odd though… given that some receptor studies have been done etc., we actually may know a fair amount about how it does what it does without actually knowing quite what it does. I.E. some 3rd person methodology data, but little 1st person methodology data.

Just to add a bit. Here is a link to Erowid’s 2C-B-FLY Vault:

( http://www.erowid.org/chemicals/2cb_fly/2cb_fly.shtml )

It has a link to Shulgin’s Tucson paper and an abstract from:

Dihydrobenzofuran analogues of hallucinogens. 4. Mescaline derivatives
Monte AP, Waldman SR, Marona-Lewicka D, Wainscott DB, Nelson DL, Sanders-Bush E, Nichols DE
J Med Chem, 1997; 40(19):2997-3008

Also found this posted on another forum in regard to 2C-B-FLY { brackets are mine}.

“There are few reports for the former {2C-B-FLY}, though Ann Shulgin spoke very highly of it at MindStates.”

Wasn’t at MindStates, but have heard something to this effect from at least 3 sources now… but again all 2nd hand.

[hugo24]

A possible Metabolite of 2c-b is 4-bromo-2,5-dihydroxi-phenethylamine which is a bit too close for my taste to the neurotoxin 6-ho-dopamin/2,4,5-trihydroxi-phenethylamine (I think theres a paper describing several of these 4-substituted 6-ho-dopamin analogs as neurotoxins).If its a problem in vivo remains to be seen.I'm aware that the primary attack is on the amine,but I have seen metabolic studies listing at least the monohydroxis.

The 2c-b-fly is in that regard an attractive alternative as the methoxis are "fixed".It might therefore be longer active a bit.

[andruejaysin]

Well from what I've read, and extending info from other fly & dragonfly compounds, I'd imagine that 2C-B FLY will be pretty much identical to 2C-B, only active at a lower dose. 2C-B DRAGONFLY might be another damp squib as it seems that the fully aromatic compounds lose a lot of their activity when taken orally.

Despite the higher receptor affinities of the DFLY compounds, I think it's the fly compounds that'll be the ones to make the impact on more widespread research

I agree, a longer acting version of the DO-X stuff seems to me making a too long thing even longer, but 2c-b,c,i, active at a lower dose, sounds like a winner. A 2c-d fly would be possible, right?

[hugo24]

The dom-fly is actually described in the 2c-b-fly article (JMC 1996,39,2953-2961), together with dob-fly and its h-analogs.Reduction of the aldehyde led to this Methyl intermediate,easy going from there to the 2c-d-fly.I guess it might have just the right duration.

2c-b-fly binds 34nm on the (ketanserin labeled rat) 5-HT2a sites,dob-fly 18nm.Theres some binding (800nm)on the 5-HT1a site with the 2c-b-fly,not unlike 2c-b (from another paper: 5-HT1a 320nm,5-HT1b 25nm,5-HT1c 36nm)

dob-fly was also tested on agonist labeled human receptors: 5-HT2a 0.48nm,5-HT2b 1.6nm,5-HT2c 0.3nm.

If the 2c-b-fly passes the broader consumer test,the alkylated versions are a must in my view,plus the tfm.Sure it seems they are just a rigified version of the normal PEA's but the jury is still out on the flys.There could be something new and unexpected evolve,so be careful.

[B9]

Having received some advice on the likely dose/effects (from a well known commentator on these matters) i am going to proceed this weekend with a trial , if it's worth writing about i shall post my impressions/dosage etc.
zophen

[crOOk]

Having received some advice on the likely dose/effects (from a well known commentator on these matters) i am going to proceed this weekend with a trial , if it's worth writing about i shall post my impressions/dosage etc.
zophen

Can't wait for your report dude.
There must be about 500 people who've tried it already and noone writes a report or at least gives some info about dosage or anything?! That's poor, really fucking poor.

crOOk

[B9]

^If you look at the 2cb fly thread in PD you'll see what i wrote about it, it's very brief but the info needed is there.
zophen.

[crOOk]

^If you look at the 2cb fly thread in PD you'll see what i wrote about it, it's very brief but the info needed is there.
zophen.

Cool, thx!

crOOk

[illuminati boy]

There must be about 500 people who've tried it already and noone writes a report or at least gives some info about dosage or anything?! That's poor, really fucking poor.
crOOk

I scoured this forum and several others and put together about 10 reports, though I posted it over in TR in hugo24’s post there. The link to that data is here:

http://www.bluelight.ru/vb/showpost....84&postcount=5

It was posted a few days ago and I have now seen reports from 100 mcg to the 38 mg. trip reported here at BL. So far, some people have had good 10 mg. experiences, but most have either pushed the dosing higher or felt that they would have to in order to reach the desired level of effects.

Hope this helps.

I B

[B9]

Tried it at 20mg this friday gone and was underwhelmed, just a bit more of the same it;s ok but well not really exciting 2ce is more interesting.
zophen.

[BilZ0r]

^ We need more drug targets.... new drugs, hitting the same receptors, = more of the same. *yawn*

[morninggloryseed]

I can't help but wonder if frequency of use influences one's outlook, expectations, and thus the final results when evaluating all of these 'new' substances.

Would someone who is quite used to tripping find 2C-B-FLY just ho-hum, while a less-experienced individual (with maybe two or three experiences) find themselves blown away with this one? Or is there no relation between frequency of tripping and how 'good' one finds various substances?

Or maybe, it could be just that 4-bromo phenethylamines pale in comparison to some of the 4-alkyl substituted ones. Or maybe a matter of dose? I myself don't find 2C-B even remotely interesting until I get to around 30mg. And even then, I've never really been very impressed. DOB and BDFL don't even sound worth the time.

[BilZ0r]

Well DOI is quite fun, and if you say DOB isn't... then lets see what differents the PDSP has to say about them.

-DOB
average 5-HT1A 5µM
Average 5-HT2A 29nM
Average 5HT2C 66nM

-DOI
Average 5-HT1A 2µM
Average 5-HT2A 45nM
Average 5-HT2C 52nM


Hmm... not hits there... shit looks the same... *shrug*

[5-HT2]

2C-b-dfly seemed pretty similar to 2C-B and DOB when I did it. Then again, I'm sure my judgement was impaired because I was coming off an adderall binge (had I been sober I probably would not have done it at the time, but I was fiending for speed and thus did what I, in my delusional state, thought was the next best thing) and eventually the amphetamine psychosis + psychedelic trip made me think I blew out part of my septum from aforementioned amphetamines. Of course, it was all a paranoid delusion and nothing was wrong with me except that I had mixed incompatible drugs. Fucking speed, it always makes me do and think shit like that.

[illuminati boy]

BilZ0r… It strikes me that while on the surface your numbers for DOB and DOI do not seem significantly different… there could be something of import there…

In the DOB data the ration of 5HT2C to 5HT2A is about 2/1 in the DOI data the ratio is about 1/1. It might be that effects depend more on the ratio between 2 or more receptors rather than absolute binding affinity alone… or not... just thinking out loud here… Would be interesting if such were the case.

I B

[morninggloryseed]

2C-b-dfly seemed pretty similar to 2C-B and DOB when I did it.

Just want to clarify if indeed you mean 2C-B-Dragonfly, and not 2C-B-FLY. If so, then can you provide more data on 2C-B-DFLY? Also, 2C-B and DOB differ in a number of ways. Are you able to highlight more as far as what about the substance resembles 2C-B, and what parts resemble DOB?

[nanobrain]

never sampled the original 2C-B, but 2C-B-FLY is rather nice in psycholitic doses.

combined w/MDMA, made me realise i really dont like the effects of MDMA anymore - that pseudo-quazi empathogenesis, grr, could not wait for it to wear off, had to take more 2C-B-FLY to sober up.

2C-B-FLY combined nicely w/ 2C-T-21.

may write a report if there is interest.

[morninggloryseed]

Any word on 2C-B-FLY, and any combinations, are of great interest. If you have the time, please submit at least a writeup!

[5-HT2]

I'm sure that I did 2-C-B-dfly.

Perhaps the request for experience reports should be mirrored in PD? It would probably get more responses there.